


Your mess is mine

by TheatricArcana



Category: Critical Role (Web Series)
Genre: Gentle Sex, M/M, Menstrual Sex, Menstruation, Morning Sex, Oral Sex, Penis In Vagina Sex, Trans Essek Thelyss, Trans Male Character, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-09-13
Updated: 2020-09-13
Packaged: 2021-03-06 17:42:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,777
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26442901
Author URL: https://archiveofourown.org/users/TheatricArcana/pseuds/TheatricArcana
Summary: Caleb takes Essek home with him, and Essek stays the night for the first time. Unfortunately, Essek wakes to a bloody surprise and has a minor freakout about it. Caleb doesn't mind so much, however.In fact, Caleb REALLY doesn't mind.(Check notes at the beginning for warnings!)
Relationships: Essek Thelyss/Caleb Widogast
Comments: 7
Kudos: 164





	Your mess is mine

**Author's Note:**

> I pictured this taking place in the Xhorhaus but I fucked up and forgot until after I made this that the sky in Rosohna is permanently dark and there is no morning LMAO. It's barely relevant though so it doesn't rlly matter.
> 
> Warning: Essek is written as a transgender man who experiences little to no dysphoria in this fanfic. I use terms like cunt/clit/breasts to describe his genitalia, and he is on his period while they have sex. Actually, period sex is like... the entire point of this fanfic. Don't read this if that bothers you.

The barest hint of morning light was visible behind the curtains, which was plenty for Essek at the moment. He wasn't sure if Caleb would have usually closed the blinds if he was sleeping alone, but he was glad Caleb thought of it last night, as Essek had been…  _ preoccupied,  _ to say the least.

The bed was soft and Caleb's body was a warm presence behind him, which eased the foul mood that Essek usually woke up in. Caleb's breath came deep and even, tickling the back of Essek's neck whenever he exhaled, so Essek knew he was asleep still. Despite being asleep, Caleb was still curled up right behind Essek, with an arm lazily thrown over Essek's waist, keeping him close. It felt safe and comforting, and Essek even briefly entertained the idea of cancelling all of his tasks as Shadowhand just to stay in bed with Caleb all day.

Essek tried to ever-so-carefully turn to face Caleb, only succeeding in rolling onto his back before Caleb's eyes were fluttering open at the disturbance. Caleb was a light sleeper, then, Essek mentally noted.

Caleb let out a soft little noise, pulling Essek in even closer before pressing a kiss onto the bare skin of Essek's shoulder.

"Good morning." Essek tried for a small smile, which Caleb returned quickly.

"It certainly is." Was all Caleb said before his lips were on Essek's.

The pace was significantly less fervent and intense compared to the kisses they had shared last night. Their movements were sleepy and mildly uncoordinated, but deep and slow at the same time. Essek was sure he was never going to tire of kissing Caleb. It felt just as amazing every time, and Essek found himself easily absorbed in the sensation, other thoughts falling away and turning into  _ Caleb, Caleb, Caleb… _

Caleb's hand shifted under the blankets, slowly trailing down Essek's abdomen. The hum of arousal found Essek much easier than it usually did, and his breath was already starting to come heavier. Essek had never been so easily undone by another being before, but Caleb Widogast was an enticing man.

"Do you have any pressing matters this morning?" Caleb asked, his voice still rough from sleep, and Essek suppressed a shiver at the sound of it.

"If I did, I'd move them." Essek replied without a second thought.

Essek reached under the sheets and grabbed Caleb's wrist before pushing Caleb's hand towards where he needed attention most. A breathless chuckle escaped Caleb at Essek's forwardness, but he certainly didn't air any complaints.

Essek let out a shuddery sigh as Caleb's hand dipped between his legs. Caleb made a pleased hum as he leaned in towards Essek's neck, mouthing at the skin there.

"This wet already?" Caleb gently teased, and Essek felt his face flush slightly as Caleb ran a finger between his folds, easily sliding across the slickness already leaking out of him. Essek honestly  _ didn't  _ get wet this easily usually, but he chalked it up to Caleb's presence simply causing his hormones to go haywire.

Essek would have responded, but Caleb slid a finger into him right as he opened his mouth to speak, turning his words into a sharp gasp.

It wasn't the best angle, really, but Caleb's fingers felt good regardless. Essek twitched his hips up into Caleb's touch involuntarily, and Caleb responded with a little nip to Essek's skin. Essek knew he should probably stop Caleb unless he wanted to wear scarves and turtlenecks for a week, but he couldn't find it in himself when Caleb started to thrust his fingers in and out of Essek, a second one slipping in easily next to the first thanks to the slick guiding the way.

Caleb sat up slightly and pulled the blanket back, making Essek shiver as his entire body was now on display and exposed to the open air.

Essek didn't miss the puzzled look that crossed Caleb's face before he slowly, almost gingerly, pulled his fingers out of Essek and just… stopped, staring down at where his hand was still between Essek's legs.

"What- Oh,  _ by the Light!" _ Essek hissed, immediately pulling away from Caleb before removing himself from the bed entirely.

Caleb let Essek go, not putting up much resistance as he looked strangely at his fingers, which were coated in blood.

_ Essek's  _ blood, to be exact.

Even Caleb's sheets had the telltale red stains, ensuring that the fabric was thoroughly ruined. Essek was sure some of the blood had several hours to set into the sheets as well, meaning that it was too late to do damage control.

Essek was  _ mortified _ .

Essek couldn't even imagine how  _ Caleb _ must feel after finally having taken Essek home with him to stay the night, only for Essek to bleed all over Caleb and his sheets in the morning. Essek could not think of a worse possible outcome for either of them.

Essek felt his temperature rise as shame and embarrassment twisted inside of him like a hot knife. Essek wanted nothing more than to simply fling himself off the top floor of his tower and forget that this ever happened, but he knew he had to at least  _ try  _ and fix this before jumping off any buildings.

"I- I  _ deeply  _ apologize for this, I had no idea that I was…" Essek trailed off, unable,  _ unwilling,  _ to even finish the sentence, so he moved on. "I can get rid of these and get you new sheets within the hour. I am truly sorry-"

As if to add insult to injury, Essek could feel even more blood begin to leak out of him and run down his thighs now that he was standing. He quickly pressed his thighs together and looked up towards the ceiling, silently cursing the gods for letting this happen to him.

"I will leave you to… To clean yourself. I'll be back for the sheets after-" Essek leaned down to start picking up his clothing, which had been discarded on the floor last night (before Essek ruined everything this morning), but Caleb spurred into motion suddenly and reached out to grab his wrist, gently preventing him from continuing.

"Essek, I think that perhaps you are presuming there to be a problem where there isn't one." Caleb said, catching Essek off guard.

"And how, exactly, is this not a problem?" Essek gestured towards the sheets and Caleb's hand, which _ ,  _ much to Essek's embarrassment,  _ still  _ had blood on it.

Caleb seemed to consider the sheets for a moment before turning back to Essek. "The sheets are… Well, the sheets actually may be a problem, but they're easily replaced. I'm afraid your presence in my bed is not as replaceable, and I'd hate to lose it right now over this. It's not- you didn't do this on  _ purpose,  _ Essek, I understand."

Essek actually did stop at this point, very carefully observing Caleb and his expression, and finding no obvious pointers that Caleb was lying to make him feel better. Caleb knew exactly what to say to quell Essek's shame, and Essek felt some of the tension ease, but...

Essek sighed.

"I think I should go home, Caleb. I need…  _ supplies  _ to deal with this and I'm sure I won't be very good company like this."

"I'm sure that between Yasha, Jester, Veth, and Beau, they will have anything you may need. I won't keep you here if you'd prefer being at home, but just know that  _ I _ prefer you here regardless." Caleb, once again, didn't appear to be lying. The kindness that Caleb had shown him while they had been together seemed to be endless, and it was almost infuriating.

Essek couldn't deny that the idea of spending his period at home, alone and in pain, seemed much less enjoyable than staying and taking advantage of Caleb's good hospitality and kindness for as long as Caleb would allow. 

All at once, Essek let the fight drain out of him.

"If you truly wish for me to stay, at least allow me to take care of the mess. I truly feel  _ awful  _ about all of this." Essek caved, because it was just so easy to give Caleb Widogast whatever he wanted, but he refused to overstay his welcome and make Caleb worry about replacing the bloody sheets.

Caleb chuckled, and then unexpectedly tugged Essek back towards the bed and pulled him down. Essek, surprised and uncoordinated, came easily.

"After we're done. It would be a shame to ruin another pair of sheets."

Caleb's lips were on his again, which was usually welcome, but Essek made a strangled noise and jerked his head back, confused and startled.

"You- Wh- What are you _ doing!?"  _ Essek hissed, trying to figure out if Caleb was  _ actually  _ implying what Essek thought he was.

Caleb looked confused, and then alarmed, immediately letting go of Essek.

"Oh, I don't think I was- Perhaps I wasn't clear enough about my- ah- intentions. I apologize, that is my fault. I should have been clearer." Caleb started apologizing, and moved back slightly from Essek, and Essek found himself missing the warmth yet questioning literally  _ everything  _ else about this scenario.

"You want to… keep going?" Essek asked, carefully.

" _ J- Ja?"  _ Caleb seemed hesitant to respond now, probably thanks to Essek's reaction. It sounded more like a question than an answer.

"It doesn't bother you?"

Caleb shook his head. " _ Nein _ , no- it is- It does not bother me so much, no. After my time with the Mighty Nein, I have grown rather used to blood."

Essek scoffed. "It is not  _ just  _ blood, you realize that, Caleb? I am- My body is getting rid of  _ chunks of my uterine lining _ . It is not an attractive process." Essek felt himself heat up at his own vulgarity, but there were only so many ways to put it while still being able to effectively communicate what was happening.

"I have eaten raw dinosaur meat by choice. I did it multiple times." Caleb stated plainly, before re-emphasizing the most important part- " _ It does not bother me,  _ Essek _. _ "

Essek opened his mouth, and then closed it, and then opened it again, a furrow in his brow as he tried to form words.

" _ Raw dinosaur meat?" _ Essek asked, perplexed and disgusted at the same time. Caleb laughed despite himself.

" _ What I mean _ is that you don't need to feel uncomfortable about this around me. I understand if you are though, and I apologize if I made you uncomfortable or upset. Just know that- ah- if you don't wish to keep going, I may need a few minutes alone to… compose myself..."

Caleb averted his gaze, and Essek realized that Caleb was actually blushing quite hard at this point. A quick glance down confirmed that,  _ yes _ , Caleb was still into this as a matter of fact.

Essek weighed his options as quickly as he could, taking a deep breath and steeling himself before he got cold feet.

"I suppose we won't have to waste any oil this way." Essek's voice came a little weaker than he'd like it to, but the meaning of his words were clear. 

"Are you sure?" Caleb looked back up at Essek, searching his face for any sign of discomfort.

"I'm sure."

Caleb hesitantly shuffled closer to Essek once more, politely giving Essek plenty of time to change his mind and back out. Essek didn't, though, instead reaching out for Caleb once he was close enough.

The slide of their bodies together was familiar now, and easy to get back into. Caleb was kissing him again, one hand wandering up and down Essek's waist, and Essek forced himself to relax.

Essek wrapped an arm around Caleb, pulling him closer so that he was on top of Essek. Essek let Caleb's weight press him into the mattress, a comforting presence above him that helped make everything else melt away. Caleb didn't put his full weight on Essek, but it was enough. Essek found himself lost in the feeling of Caleb's lips against his own, and he hummed contentedly when he felt Caleb roll his hips lazily, grinding his cock against Essek.

Caleb broke the kiss to start mouthing at Essek's jawline and neck, occasionally sucking marks into Essek's skin, which Essek still did not stop Caleb from doing.

Caleb's kisses trailed down his collarbone and to his chest, making Essek twitch his hips in excitement as he urged Caleb to continue.

A hot tongue dragged across Essek's nipple before wrapping around it. Essek sighed shakily, letting his eyes flutter shut as he soaked in the attention and pleasure that Caleb provided. Essek had never thought of his chest as being particularly sensitive, but it was different when Caleb was touching him. Now he had to fight to keep his breathing even and steady, unwilling to let Caleb know just how easily he was affected by Caleb's actions, but that only made Caleb more eager to get a reaction.

A noise of surprise escaped Essek when Caleb turned his attention from one breast to the other, except this time he gently closed his teeth around Essek's nipple, the tiniest hint of pain that made Essek shiver and tense. Caleb let go quickly, however. He wouldn't actually hurt Essek, especially not right now.

Much to Essek's surprise, Caleb's kisses continued to trail lower, down his ribs and stomach and towards-

Essek startled and propped himself up on his elbows as he realized what Caleb was leading up to, reaching a hand out to stop him. "Caleb, you aren't  _ actually _ going to-?"

"Raw dinosaur meat." Caleb reminded him, before pressing his tongue against Essek's clit.

Essek actually jumped at the sensation, his nerves running haywire and telling him that he shouldn't be doing this even though he knew it was okay. Essek didn't actually tend to touch himself while he was on his period, so the feeling was foreign and somehow different than other times. His reactions didn't go unnoticed by Caleb, who was grinning far too much for Essek's liking.

"More sensitive like this,  _ ja _ ?" Caleb teased, but didn't give him a chance to respond before his tongue was back on Essek.

Essek moaned properly this time, bucking his hips up towards Caleb's face, chasing the wet heat of Caleb's mouth. The ache that had started to settle into his stomach slowly lessened as Caleb lapped at his sensitive folds just as eagerly as he had the night before. It was too much to watch, and Essek let his head fall back towards the pillows as he threw an arm over his face.

Caleb carefully rolled his tongue against Essek's clit, presumably following a pattern that Essek couldn't. The hot, steady pressure was better than anything Essek could do to himself, and he was suddenly very glad he decided to stay.

Caleb dragged his tongue downwards, licking around Essek's cunt before pressing his tongue  _ in,  _ as if Essek wasn't bleeding at all. Essek's thighs trembled when Caleb's hot tongue spread him, sliding out slowly and then back in enough times that Essek lost count. 

At some point Caleb raised his head up to return his attention towards Essek's clit, but Essek was caught off guard and laughed at the view before he clamped a hand over his mouth to stop himself.

Caleb had blood smeared across the tip of his nose, like the worst clown Essek had ever seen.

"What is so funny?" Caleb asked, brow furrowed as he looked up at Essek, who was still trying not to laugh.

"You, ah-" Essek started, before shaking his head with a small smile across his lips. "Just let me."

Essek sat up enough to reach Caleb's face before using his thumb to wipe the majority of the blood off of Caleb's nose. Caleb let out a little laugh himself as he realized what Essek was doing.

"My apologies, I've been told that I am a messy eater." Caleb grinned sheepishly, like he was afraid the joke wouldn't land, but Essek immediately burst out into laughter again, which was a lovely sound to Caleb.

Essek's laughter turned into a breathless moan when Caleb returned to his previous task, laving against Essek's clit like nothing had happened.

Essek let out a sharp, high-pitched moan when Caleb wrapped his mouth around Essek's clit and  _ sucked _ . Impulsively, Essek tried to close his thighs, but Caleb held them open easily with how much Essek was shaking.

It was pathetic how easily Essek fell apart under Caleb, but Essek didn't care, too distracted by the pleasurable heat building inside his stomach as Caleb sucked and licked at his clit. Caleb was an attentive lover, and he recognized all the little changes in Essek's body language when he did something right. Caleb easily committed to memory any sweet spots as well, making it easy to work Essek to the edge.

Essek's thighs spasmed and he cried out something that sounded roughly like Caleb's name, curling in on himself as he shuddered and came hard.

Caleb was no longer sucking or licking at anything, instead using his tongue to apply gentle pressure to Essek's clit as he rode out his orgasm. Caleb could even feel Essek's cock throbbing under his tongue as he came down, which made his own twitch as well.

After Essek seemed to have caught his breath, Caleb pulled away from Essek and sat up, revealing that his beard was coated by a layer of blood and slick. Essek couldn't help but wrinkle his nose in disgust, even though it was his own blood, and Caleb let out a little huff of laughter.

"That bad?" Caleb grabbed the already ruined sheet and used it to wipe off some of the blood, which was incredibly unclassy, but Essek supposed everything they were doing at the moment was unclassy.

"I love you and I appreciate what you do for me, but you are not kissing me until you brush your teeth." Essek wondered if maybe that was rude to say, but Caleb was the one who consented to getting blood in his mouth, not Essek.

Caleb laughed. "I knew you would say that."

Caleb grabbed Essek by the hips and pulled him closer, which was an easy feat with how light Essek was. Essek shivered when Caleb cupped his dripping, bloody heat with a rough, callused hand.

"Are you still up for more, though?" Caleb asked, as if Essek would leave him hard and wanting after Caleb was so generous to him.

"Of course." Essek's voice came out a little breathier than intended, which Caleb thankfully didn't comment on. 

Caleb removed his hand from between Essek's legs, using the blood and slick that had gotten on his hand to stroke himself a few times, which Essek couldn't tell if he was disgusted or turned on by.

There was a brief pause as Caleb lined himself up, glancing up at Essek and waiting for that one last little nod, which Essek gave without a second thought.

Caleb locked eyes with Essek before sinking into him, blood and slick guiding the way.

Essek felt  _ full _ , almost aching with it. He was always sore and sensitive during this time of the month, and he was aware of that now more than ever thanks to Caleb being inside of him. The fullness was a welcome sensation, but Essek could easily picture the pleasure fading if Caleb moved too roughly. 

Essek moved to slowly wrap his arms around the back of Caleb's neck, pulling him closer carefully. He mouthed at the skin on Caleb's neck and shoulders, stubble scratching his face whenever he went too far up Caleb's neck.

"Please, be gentle?" Essek breathed against Caleb's skin.

"Whatever you need,  _ meine liebe." _

It was a slow, lazy pace. Essek enjoyed the feeling of being close to Caleb just as much as he enjoyed Caleb's tongue. Being intimate with someone he truly trusted was better than he could ever put into words, and it felt silly to chase another orgasm when he already had all the pleasure he needed by simply letting Caleb roll his hips against him, unhurried and unrushed.

Caleb wrapped his arms around Essek, but was careful not to put all of his weight on Essek even as he pressed their bodies together more firmly. Usually Essek wouldn't care, but the idea of all that pressure and weight on his abdomen sounded uncomfortable at the moment. Thankfully, Caleb seemed to know better without Essek having to tell him. Essek briefly wondered if perhaps Caleb had done this with someone else before, but it wasn't a thought with any bitter feelings attached- just a momentary curiosity that faded away with each second he spent in Caleb's embrace.

Essek purposefully clenched down onto Caleb a little, and Caleb made a strangled gasping sound next to Essek's ear, his hips stuttering slightly before continuing pace.

Essek buried his face into the warm skin of Caleb's shoulder, occasionally licking and sucking at the freckled skin he found there between soft, shaky moans and shuddering gasps. He slid his hand up the back of Caleb's neck, threading his fingertips through Caleb's long, red hair and soothingly scratching the back of Caleb's head with his fingernails.

It was pleasurable enough that Essek was pretty sure he could bask in the feeling forever. He wanted to spend every morning for the rest of his life with Caleb, exactly like this. Maybe Caleb would get tired of it, but Essek was fairly certain that he would always love this just as much as he did now.

Essek noticed when Caleb's leisurely thrusts started getting a little less so, Caleb's hips occasionally stuttering in their controlled motions before continuing. Caleb did pick up the pace a little at some point, but it was never enough to cause Essek any discomfort, still well within the range of being gentle.

Eventually Caleb thrust into Essek one last time before he gasped wetly next to Essek's ear, fingers spasming on Essek's waist as he shuddered through the pleasure. Essek deliberately provided a few encouraging squeezes as Caleb spilled inside of him, which made Caleb's thighs twitch every time.

Caleb stayed there for several minutes, and it was far from Essek to complain about it. In fact, a displeased sound escaped him when Caleb finally untangled them from each other.

Caleb looked around, as if assessing the damage, and Essek joined him.

Caleb's hands would need to be scrubbed, and the sheets were absolutely beyond help. There was a bloody mess of cum and slick between his thighs, they were both coated in a layer of sweat, and Essek felt  _ amazing _ .

Essek was glad he stayed.


End file.
